5-(Bromomethyl)-3-methyl-1,2-oxazole
[CAS# 36958-61-9]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 5-(Bromomethyl)-3-methyl-1,2-oxazole
• Molecular Formula: C₅H₆BrNO
• Molecular Weight: 176.01
• CAS Registry Number: 36958-61-9
• EC Number: 687-945-8
• SMILES: CC1=NOC(=C1)CBr

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 225.4±25.0 ºC 760 mmHg (Calc.)^*
• Flash point: 90.1±23.2 ºC (Calc.)^*
• Index of refraction: 1.526 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314-H318
• Precautionary Statements: P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318

Discovory and Applicatios

5-(Bromomethyl)-3-methyl-1,2-oxazole is a heterocyclic compound characterized by an oxazole ring substituted with a bromomethyl group at the 5-position and a methyl group at the 3-position. The presence of the bromomethyl moiety provides a reactive site for nucleophilic substitution, while the methyl group influences the electronic properties and steric environment of the ring, making this compound a versatile building block in organic synthesis.

The compound can be synthesized by selective bromination of 3-methyl-1,2-oxazole derivatives or through condensation strategies involving α-bromo ketones with suitable nitrogen and oxygen sources to form the oxazole ring. Control over reaction conditions such as temperature, solvent, and stoichiometry is crucial to achieve high regioselectivity and to minimize side reactions, including polybromination or ring degradation.

5-(Bromomethyl)-3-methyl-1,2-oxazole is primarily used as an intermediate in medicinal chemistry and heterocyclic chemistry. The bromomethyl group is highly reactive toward nucleophiles such as amines, thiols, and alkoxides, allowing the introduction of diverse substituents at the 5-position. This reactivity is often exploited in the synthesis of pharmacologically active molecules, including enzyme inhibitors, antiviral agents, and ligands for receptor studies.

The oxazole ring is an important heterocyclic scaffold in many bioactive compounds. Its aromaticity, nitrogen-oxygen functionality, and planar geometry facilitate interactions with biological targets through hydrogen bonding, π-stacking, and dipole interactions. The methyl group at the 3-position can modulate binding affinity, lipophilicity, and metabolic stability of oxazole derivatives, making 5-(Bromomethyl)-3-methyl-1,2-oxazole a valuable starting material for drug discovery.

In addition to pharmaceutical applications, this compound is used in materials science for the preparation of functionalized heterocycles, fluorescent probes, and cross-linked polymers. Its reactive bromomethyl site allows attachment of molecular moieties to solid supports or incorporation into polymeric chains, contributing to the development of functional materials with tailored properties.

Physically, 5-(Bromomethyl)-3-methyl-1,2-oxazole is typically obtained as a crystalline solid or an oil, depending on the purification method. It is soluble in polar organic solvents such as dichloromethane, dimethylformamide, and acetonitrile. The compound is sensitive to moisture and light, which can lead to hydrolysis or decomposition of the bromomethyl group, so it should be stored under anhydrous and inert conditions.

Overall, 5-(Bromomethyl)-3-methyl-1,2-oxazole is a versatile heterocyclic intermediate. Its combination of a reactive bromomethyl group, a substituted oxazole ring, and a small lipophilic methyl substituent enables diverse chemical transformations. This makes it an important building block for synthetic organic chemistry, medicinal chemistry, and materials science research.

References

2005. Synthesis of 5-Bromomethylisoxazoles and Their Reactions with Secondary Amines. Russian Journal of Organic Chemistry, 41(8).
DOI: 10.1007/s11178-005-0314-8

1973. Reaction of 1-bromo-1,2-pentadien-4-one with some nucleophiles. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 22(6).
DOI: 10.1007/bf00928595